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“Well do you want me to be your boyfriend tonight?” The boy asked giving Jeffrey a wink.

“Umm, no thanks.” He quickly responded as he began walking again to get out the situation.

“Ouch! Dissed!” the other boy teased his friend.

Oh my gosh! They really did think they were talking to a girl! He passed!!! He closed his eyes for a moment and made up his mind to be at ease. He looked like a girl and he had to act like one to if this was going to work.

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Admin Note: Originally published on BigCloset TopShelf on Tuesday 07-27-2009 at 1:22 pm, this retro classic was pulled out of the closet, and re-presented for our newer readers. ~Sephrena
 

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Greg and Kimberly had what is commonly thought of as the All-American family. Greg was the bread winner working for, well, a bakery. He did not make a lot of money but enjoyed what he did while providing an adequate life for his family. He and Kimberly had been married for 18 years and had 5 lovely children ranging from Greg Jr at 16 years old to Jenny at 3. Kimberly was a stay at home mom and absolutely loved that calling. She always wanted a big family and although it was very challenging at time, she would have it no other way.

Little Jeffrey fell right in the middle of the bunch. He just turned 11 and was a rather quiet boy although this was not always the case. Greg & Kimberly remembered when Jeffrey was a ball of energy who would rattle off questions and chat like there was no tomorrow. He was so rambunctious and had a real zest for life. For the last couple years, however, he had become very introverted and sullen. That happy boy of yesterday was replaced with a depressed soul.

Of all their children, Jeffrey was the one who most concerned them. They tried everything to try to get him in better spirits with little success. He just seemed like he was in a rut.

Greg attempted to get him involved in sports but Jeffrey wanted nothing to do with that. He was not interested which was made very clear by his lack of participation.

Jeffrey took on a “goth” look about a year ago and had developed quite a collection of black clothes. Kimberly did not believe in inhibiting her children’s self expression although she hoped that Jeffrey’s gothic phase was one that he would grow out of quickly. He even convinced his mom to let him dye his hair black and donned the black eyeliner several times with dad squirming in disagreement.

Greg was indeed feeling frustration with his son and the direction he was headed. It wasn’t just the anti-social look that bugged him; it was Jeffrey’s I-don’t-care attitude that pushed his dad’s buttons. Jeffrey did not show any interest in anything that his family was in to. He was like the black sheep who was quickly separating himself from the group.

Kimberly would often share Jeffrey’s issues with her sister Marge. Marge was always a good sounding board with her very liberal attitude and great sense of humor. It would always amaze Kimberly how unphased Marge would be over things that her and Greg felt were such big problems with Jeffrey.

“Why don’t you let me take him for the summer? He and I would have a great time.” Marge said over the phone.

“Oh he would drive you crazy after the first day Marge. He is just so distant lately. He seems so sad and upset with life. We are really thinking about getting him some therapy.”

“Yeah, that would be great sis, send him to a shrink. That will be fantastic for his self esteem.” Marge retorted. “Let him stay with me for a month or two. He just needs a change of pace and you know that I can give him that. Let me see if I can help him and then send him to therapy if that doesn’t work.”

“You are being serious?” Kimberly asked.

“Of course I am. It gets lonely here. I would love to have some company.”

“Well, let me talk it over with Greg and Jeffrey. It might be just what he needs.” Kimberly replied.
 
 
That night she discussed to thought with her husband.

“You really think that it would be good for Jeffrey to be away from the family for that long?” Greg asked.

“You know how Marge is. I think it would be very good for Jeffrey to experience something new. Some time away may be just what he needs. I think it would be a great adventure.”

“I’m fine with it dear. How do we convince him though?” Greg asked.

“I already talked to him. He was apprehensive but admitted that he didn’t care to go on our family vacation so he accepted.”
“Well I guess it’s set then. When does this happen?”

“We have to book a flight, but Marge is ready when we are.”

Jeffrey knew Aunt Marge. She was a cool woman although a little strange. She was a few years older than his mom, wasn’t married and didn’t have any kids. She lived in a very small town in southern California and painted for a living. He figured staying with her for the summer would be way better than having to do the usual road trip with his family. Maybe she would just leave him alone.
 
 
A couple weeks later, Jeffrey was standing in Marge’s loft. Admittedly it was a very cool place to live. She had all of her art stuff everywhere. Easels, big poster boards, paint splattered here and there.

“So what do you think of my humble abode?” she asked.

“It’s ok”

“Fair enough. So what do you enjoy doing?”

“Not much.”

“Well, maybe we can find some new things for you to do then”

“Highly unlikely.”

“Let’s see…there’s a lake just down the way. You can fish there and they have some rope to swing on.”

“I don’t like swimming.”

“Hmmm, ok. How about art? I could teach you a lot of things.”

“I don’t like drawing.”

“Gotcha. You are a tough nut to crack. Maybe we’ll just get you settled in and once you get comfortable here we can find you things to do.”

“Sounds good” he replied in a sarcastic tone.

She graciously showed Jeffrey to his room and he set up camp. He wondered if maybe this was a mistake. His aunt seemed way too eager to please and he hoped that by giving her the cold shoulder she would tone it down and leave him alone soon.

What Jeffrey didn’t realize though was that his aunt Marge was an equally tough nut to crack.
 
 
A week went by and Jeffrey showed very little interest in any of his aunt’s ideas. Why couldn’t she just go on with her life and let him veg in his room?
Marge was having regular talks with Jeffrey’s mom.

“So has he come out of his shell with you?” Kimberly asked.

“Not yet, but he will soon. I’m just trying to figure that kid out. He’s a tough read.”

“No need to tell me. We have been pulling our hair out trying to understand him.”

“I love the challenge sis.”

“Well if you can get him to find some happiness during his time with you I’ll owe you big.”

Marge knew she could break Jeffrey’s shell and she just had to find the right angle. She wished that he would just open up to her and tell her what was up with the poor attitude. She knew that they had to be something under the surface that was bothering him. Marge kept a keen eye out for anything she found that seemed to spark Jeffrey’s interest. When she was painting he didn’t give her the time of day. He had no interest in preparing lunch or dinner so she didn’t have a future chef on her hands. Hmmm. She couldn’t get him down to the lake yet but still kept that idea alive.

“So do you have any plans today? Marge asked Jeffrey as they sat on the couch one morning. She would pull out her make-up case every day at this time to apply her face.

“Nope.” He replied.
“Do you want me to come up with some good ideas? I’m full of them.” She replied as she applied her foundation.

“Nope. I’m good.”

“You know this is going to be a very long summer if you just sulk around the house every day.” She stated as she brushed her eye shadow on.

“Yep. That’s how I like it.”

Marge opened her eyeliner cap and glanced at Jeffrey not understanding his dismal response. She noticed him intently staring at her. Was there interest perhaps?

“Now that can’t be true sweetie. This is a no sulking household.” She said and she lined her eyes with the black ink. He was staring again…could her applying her make-up be interesting to him? Strange, but maybe. He was always around when she put on her makeup.

“So, your mom told me that you sometimes really do yourself up with that goth look. Do you use this type of eyeliner?” Marge asked trying to see if she could coax something out of him.

“No, when I did it I would use a sharpie.”

“A sharpie? Oh dear! That is not at all good for you Jeffrey. You could injure your eyes.”

“It never did anything bad. It just took a while to get off.” He replied with a little spunk.

Marge could tell by the tone of his voice that Jeffrey was into this conversation. She would take it further.

“Do you want me to “goth” you up?”

“With your makeup?” Jeffrey asked.

“No, with my collection of permanent markers. Of course with my makeup silly!”

“Look I’m no sissy alright?”

“I didn’t even think that. Let me show you what I can do ok?”

“Ok, but you better not make me look stupid.”

Marge had Jeffrey sit next to her on the couch. She was reading a lot of interest in him.

“Ok, close your eyes.”

Closing his eyes Jeffrey could feel a wet substance being applied to his upper lids.

“Good, now give it a second to dry. Ok, now look up and tilt your head back a bit. Perfect.”
 
 
The wet substance was penciled unto his bottom lids as well.

“Wow, that looks very dramatic. Do you want to see?” Marge asked.

“Ok”

She held up a hand mirror for him to see. She could tell from his reaction that he was mesmerized by how he looked.

“So?”

“It looks way better than how I did it.” He replied.

“Well that’s because I am very good at makeup.” She stated noticing that Jeffrey seemed to spark to life all of a sudden.

“Do you want me to show you some other tricks?”

“…Nope.” He replied with a little hesitation.

“Oh come on, did you ever do anything else for the goth look?”

“A couple of times I colored my lips black.”

“What did you use for that pray tell?”

“Some Halloween stuff”

“Let me try something on you. It’s not black but it’s a really deep red. It may make you look like a vampire” Marge urged him.

Jeffrey was unsure.

“Here, give me your lips.”

She deftly removed the top of the tube of crimson lipstick and spread it on his lips.

“Now rub your lips together. Good. Here, blot them on this tissue. You look way cool now!”

Jeffrey lifted the mirror once again and his eyes widened.

“You are making me look like a sissy!” He retorted.

“Not at all sweetie. I’ll take it off ok?” She replied noticing how he couldn’t take his eyes off himself. She had been around enough boys to know that the normal reaction would be to pull down the mirror and immediately rub the lipstick off with their hand. Jeffrey however was transfixed on his reflection even though he acted
like he was offended.

“I’m just having fun. You haven’t allowed me any of that since you arrived so just this once let me have my moment please?” She pleaded reading that he really didn’t want her to remove the lipstick.

“Your idea of fun is putting makeup on me?”

“Oh Jeffrey, your sister has never used you as a makeup canvas?”

“No!”

“Please please please let me do you face up just this once? I promise I won’t tell anyone.”

“No way!” he replied.

Once again, the reaction wasn’t that of a typical boy. It was almost like he was acting like he was upset. The emotion wasn’t real.

“Ok, let me have my fun and I promise you that I will leave you alone this whole week. Deal?”

This would be the deal breaker. If her hunch was correct he would let her do his makeup. Otherwise, maybe she was way off base.

“Well it would be worth it to get you out of my hair.”

“So it’s a deal?”

“Ughhh, deal”

Marge clapped her hands in delight. She could swear that he was way more into this than she was and had to see if her hunch was correct.

“Alright, now you can’t look in the mirror until I’m done ok?”

“I can’t believe how excited you are about this.”

“Yes, this is how I have fun alright?”
 
 
With that she proceeded to apply a light coat of foundation.

“This will even out your skin and make it look smooth.”

“I don’t care.”

Marge giggled and she powdered his face.

“That stuff stinks.” He stated.

“I like the way it smells but it does have a certain odor I guess.”

“Close your eyes.”

She used a brush on his eyelids staring with light beige and gradually add layers of darker browns.

“I’m giving you some smoky eyes. You’re gonna really look goth.”

“Now look up again.”

Marge pulled the brush and lacquered the thick black substance unto his top lashes followed by the bottom.

“Wow, you have really nice eyelashes. I wish mine were that long”

“Yeah yeah yeah”

She then proceeded to use a lip liner to define his lips a little more and develop a pout look.

“I am floored Jeffrey. You look so amazing. I know that you are not a girl but you really look good with makeup on”

“I hope you are having fun at my expense.” He replied feeling embarrassed.

“Here look”

She closely observed his reaction to the reflection.

“I look like a freaking girl.” He stated with an angry tone.

“Well it was fun for me. Thank you for indulging my weirdness.”

She noticed that he could not take his eyes off of himself. There was definitely something there.

“Well you can run along now. I won’t embarrass you any more.”

“Thank you very much” he said sarcastically as he left for his room.
 
 
Marge thought about what had just happened. Was she crazy? Jeffrey seemed engulfed in what was going on. The nervous looks on his face were not that of dislike. They looked more like a longing that was being satisfied. There was embarrassment there but was that due to him not being sure what she was thinking. Maybe he was afraid of what she may say or how she might judge him. In any case, Jeffrey had not shown this much life since he had arrived.

A couple hours later she called him to the dining room to have supper.

Her jaw dropped.

“Oh honey, you didn’t have to keep that makeup on. I figured that you would wash it off.”

Jeffrey became very embarrassed.

“Well, I didn’t know how to…you should have showed me how to take it off. Now you can laugh at me some more.”

“Oh honey, I’m not laughing at you. I’m happy you didn’t wash it off. Now I can observe my handwork once more.” She joked in a sympathetic way.

“Do you want me to show you how to wash it off?”

“Uh yes of course I do.”

“Ok…we can do it now or do you want to wait until after we eat?” she asked.

She was surprised that he didn’t take off the makeup. A normal boy would have rinsed that stuff off immediately. He was obviously embarrassed from her initial reaction. She would have to show him that she was open to anything.

“Whatever.” He replied with some attitude.

“Ok, let’s wait then”
 
 
As they enjoyed dinner, Marge tried to calm his nerves.

“You know you should let me practice on you more often. You make a great canvas.”

“Yeah so you can laugh at me?”

“Not at all. I don’t see anything wrong with a boy wearing makeup.”

“Really?”

“Really. Trust me, I’ve seen it all and you in makeup doesn’t faze me one bit.”

She could see Jeffrey sigh in relief. He enjoyed wearing the makeup. She was certain.

They finished up dinner.

“I got a couple netfliks movies if you want to watch them. I’ll make some popcorn and we could have a movie night.”

“Ummm Okay.”
 
 
His attitude was swinging. This was the boy who spent all his time in isolation in the bedroom and now he was open to actually spending time with her?

“You wanna get that makeup off?”

“…Okay” he hesitated. She saw his mood switch from uplifted to sad in a split second.

“or we could wash it off before you go to bed tonight. Then you would only have to wash you face once.” She offered.

“Would that be better?” he replied as his mood lightened once again almost urging her to say yes.

“Yes, then we could take off our makeup at the same time.”

They sat down and watched movies back to back. She was amazed at how lively Jeffrey was. The boy who was so depressed and self loathing was now laughing and genuinely enjoying the evening. This was a milestone.

He was glowing and looked so at ease with his face all made up.

After the movies she showed him how to wash all the makeup off and said goodnight. He proceeded to do something that was unheard of. He gave her a big hug.

“Well that was nice” She said, “did you actually have fun today?”

“Yes” was all he said.
 
 
The next morning found Jeffrey in particularly good spirits. He was up for breakfast and even helped a little by toasting the bread.

“Did you get a good night’s sleep Jeffrey?”

“Yes I did. Those movies were great last night.”

“So we found something you like doing…good. I’ll let you look at the list of movies to choose from and we can do that more often.”

“That would be awesome.”

Marge was amazed at how his attitude had switched so dramatically overnight. She knew that his wearing makeup had something to do with it but knew that she would have to take it slowly to keep him from clamming up.
 
 
After breakfast Marge took a shower and sat on the couch as usual to put on her face. Jeffrey was sitting there watching tv.

“I am shocked.” Marge stated.

“Why?”

“I promised I would leave you alone for the rest of the week and you are sitting out here. I figured you would be in your room doing whatever you do in there.”

“It’s ok. I may use it still but I kind of like hanging out with you.”

“You do? That really makes my day sweetie!” Marge gushed as she gave him a big hug. Real progress was underway.

Marge began putting on her makeup and she could see right away that Jeffrey’s attention focused away from the TV and unto her. She would have to delve deeper.

“So I’m sorry if I embarrassed you yesterday by putting makeup on you. You were a great sport though.”

“Oh…it’s ok. You seemed like you were having such a fun time doing it. “

“I was having a blast. How did it feel being all done up?” She joked.

“It was weird I guess.”

“Well I promise I won’t torture you like that again.” She replied paying close attention to his reaction.

“Good! Like I want to look stupid like that again!” He angrily sneered.

She noticed how drastically his demeanor had changed. He looked so upset as he folded his arms and turned back to the television. A normal boy would not be like this. What if she steered the conversation back to make-up?

“Well I don’t think you looked stupid at all for what it’s worth.”

She saw a glimmer.

“You don’t?”

“No sweetie, you looked adorable.”

“A boy wearing make-up is adorable to you?”

“I have no problem with a boy wearing make-up. If you couldn’t tell by now, I’m a very open minded person so you wearing make-up is not going to faze me.” She replied and then let him have it, “Let me ask you something Jeffrey…did you like me putting makeup on you?”

He paused for a moment not knowing what to say.

“Look honey, I’m not going to judge you. If you liked wearing makeup then open up and let me know. Here’s your chance.” She offered.

“No, I didn’t like you putting makeup on me. I did it because you promised to leave me alone so leave me alone!” He yelled as he jumped off the couch and stormed to his room.
 
 
Marge sat there stunned. Was she wrong? She so thought that she was on to something. She was convinced he just needed time to reflect. She had just finished up her makeup wondering if she should go and comfort Jeffrey. She decided to let him be.

It was about 20 minutes later that Jeffrey nervously approached her.

“Hey sugar I’m sorry I upset you…” she started before being interrupted by Jeffrey.

“I liked you putting makeup on me.” He blurted out briefly closing his eyes as if to avoid the pain of embarrassment.

Marge simply stood up, walked over to him and gave him an enormous hug. She knew how much courage he had to muster up to reveal that to her.

“Listen closely Jeffrey, I want your summer here to be a great one. When you arrived you seemed so unhappy and I didn’t know what I was going to do to brighten your mood. All that changed last night. Open up to me sweetie. I know it was very embarrassing to admit that. You won’t get many opportunities like this in life so take advantage of it.”

He felt so warm and comfortable.

“So we found out that you like wearing makeup. I’m excited! Do you know how boring it gets having to do up the same face every day? Now I have a makeup buddy!” She exclaimed really trying to ease the tension of this whole situation.

“So you don’t think it’s weird that I like makeup?” Jeffrey pressed the issue.

“Sure it’s a little weird but who wants to be normal? Let me tell you, normal is usually boring.”

“I guess so. You’re not going to tell my parents are you?”

“Your mom gave me a very long leash with you this summer. They are concerned with your outlook on life lately and wanted you to get away for a whole to find yourself. I will keep this between you and I.”

That alone gave him such a secure feeling.

“So shall we make up your face today?” She asked.

“Ummmm, ok.”

“Alrighty then. Go ahead and sit down.”
 
 
Marge proceeded to do Jeffrey’s makeup once again. She could see him loosening up more and more as she went along.

“So I’m curious, where does this fascination with makeup come from?”

“I don’t know. I like the colors and looking like someone else I guess”

“Yeah, the colors are fun and the style variations are endless.” She replied as she finished up his face.

“Do you mind if I do something with your hair?”

“Like what?” he asked with a bit of defense.

“Just trust me ok?”

He replied with a nod. His hair was of pretty long for a boy. She brushed his hair a bit, parted in on the left side and placed a pink barrette on the right side. It was simple but cute she thought. Marge was curious as to how he would feel about the barrette.

“Ok, all done!” she said handing him the mirror.

He looked at himself in silence. The expression on his face said enough.

“So?” she compelled him.

“I really like it! It looks good.” He gushed. He found it hard to contain his excitement.

“How do you feel about the barrette. I thought it was a nice touch.”

“I love it! I like it how it keeps my hair out of my eyes.”

“Sweetie, you seem to be a different boy since I played around with makeup.”

“What do you mean?”

“Well you have gone from a depressed, quiet boy to a very happy, bright boy. I think we have found something that makes you very happy.”

He didn’t say a word but didn’t deny it at all. She had to find out how far this fascination with female things went. Was it just with makeup and barrettes or did it extend to clothing?

“So Jeffrey, I have an idea. Since you are all done up and looking fantastic, why don’t we finish the look and play around with your clothes?”

“Play around how?”

“Well let’s go into my bedroom and see what we have ok?”

“Ok” he replied in a sort-of trance like state.
 
 
Marge led him into her bedroom and had him sit on the bed.

“Alrighty, I’m thinking of something like this maybe.” She stated as she removed an electric blue dress from her closet.

“A dress?!?” Jeffrey asked acting a little shocked.

“Yes, I just thought that you might want to try one on and see how it looks.”

“Seriously, a dress?” He replied once again trying to act like he wasn’t interested.

“We don’t have to…I just figured it might be fun.”

“…Just this once then.” He whispered.

“What?”

“I said just this once ok?!?”

“Yipee!” Marge replied. Although he was playing hard to get she could read the expression on his face. He so wanted to put on that dress.

“I want you to just let me do what I do. I know you are doing this reluctantly but let me have my fun. Will you trust me?”

“Take this dress into the bathroom and put it on. You’ll want to remove your clothes.”

Jeffrey took the dress into the room and quickly took his clothes off with the exception of his underwear. His heart was racing. He unzipped the back of the dress and stepped into it pulling the straps up around his shoulders. He attempted to zip it up but could only manage half-way.

He caught his reflection in the mirror. He was beautiful. Was that really him? He looked so different.

“How does it look?” Marge asked.

“Alright I guess.”

“Well come out here and let me see.”

“I’m embarrassed.” He replied being very reluctant to let he see.

“Oh come on Jeffrey. I thought we were buddies by now.”

A few seconds went by and then the door slowly opened. Jeffrey stepped out of the bathroom looking quite amazing in the dress.

“I couldn’t get the zipper up in back.”

“Tell me about it. Some designs are so not functional. Here let me help.” She replied as he turned around for her to zip him up.

“This dress fits you really well…you look pretty!” she claimed using the feminine word.

“Thanks. It feels weird just having an opening.” He replied nervously.

“Well it’s nice in the summer when you get a cool breeze shooting up.” She said trying to calm the anxious boy.

“Here try on these” she said handing him a pair of mary-jane shoes.

He slipped them on and she helped buckle them.

“Go ahead and walk around a bit and see how you feel.”

He walked around the room not quite sure how to act. He was so anxious and nervous.

“Well don’t take this the wrong way but you look beautiful!” Marge stated.
 
 
It was very clear to her that he was in heaven. The look on his face said it all. He had an almost longing, yearning expression in his eyes. It was as if he was complete.

“What’s wrong sweetie?” she asked. His eyes were tearing up as he plopped himself on her bed.

“I’m not a freak ok?!” he said and he began crying heavily.

“Oh dear, I am not here to judge you at all” she replied giving him a huge hug, “you really feel comfortable dressed like this don’t you?”

With a big exhale of breath he replied, “yes…”

“Do your parents know anything about this?”

“No, please don’t tell them. They would kill me” he pleaded.

“Shhhh, I won’t sweetie. Is this why you are so withdrawn and sad all the time?”

“Yes. I don’t know how to deal with it and there’s no one to talk to.” He admitted as he continued sobbing deeply.

“You have me now ok? Listen to me. You can tell me anything. I won’t judge you.”

“That makes me feel so good” he replied squeezing her tight.

“Honey, do you want to be a girl? Is that what is bothering you?” Marge asked.

“Yes, I think so…”

They sat there in silence for several moments. Marge realized how much courage that must have taken to admit. That poor boy. He must have been so miserable having to keep those feelings inside with no one to talk to. He was crying out for help now and she would have to do her part.

“Ok, wipe those tears honey. You’re here for the next 2 months so why don’t we try having you live it as a girl and see how it feels? If you try it and don’t like it then it will be just between us and if you decide this is who you really are then we will think of something ok?”

“You would do that for me?” Jeffrey asked. He was taken aback by her liberal attitude.

“Of course I will. Like I said before, I want this to be a great summer for you. I think that you need to delve into your feelings and see if this is who you are.”

They hugged once again and decided on what would happen. Jeffrey would live as a girl at least around the house. If at any time he didn’t want to anymore he could quit. Marge promised to treat him just like a normal girl including calling him “Ashley”, which turned out to be a name that he was fond of for some time. The next day the two went shopping.

“Shall we go shopping?” Marge asked the nervous boy.

“For clothes?”

“Of course. We need to buy you some essentials.”

“Ok” he replied with trepidation.

“Do you want to go as you are now or change?”

“Change…I don’t want to go outside like this.”

“Ok, go ahead and wash off your makeup and change. “
 
 
Jeffrey quickly washed his face and switched back to his regular clothes. His heart continued to beat a million miles an hour with a sense of euphoria.
She took him to DIllards and headed straight for the misses department.

“First things first, which of these do you like” she asked him as they viewed the selection of panties.

“Could you not be so loud’ Jeffrey replied feeling embarrassed at how nonchalantly his aunt acted.

“Sorry, which ones do you like?” she quieted down.

He tried to overcome his nervousness and relax a little as he observed the different style and colors. His eyes drew to the low rise bikini cut panties. They were in a 6 pack and ran a gamut of different soft, pastel shades. He pointed to them.

“Go ahead and grab them.”

He pulled them off the hook and quickly placed them into the shopping cart.

They strolled over to a rack containing a multitude of bras.

“I don’t really need one of those do I? I mean I don’t have anything there.”

“You’re 14 honey and girls your age have some breast development so I would say that you do. We can figure out how to fill them out.”

Once again Jeffrey looked over the bras and selected three. One was plain white with a little pink bow in the middle, the other was a tan color that had removable straps, the third was a black bra with quite a bit of lace. Marge gave her nephew some advice on each selection.
 
 
Next they moved over to choose several selections of shorts, jeans, dresses, skirts and blouses. Jeffrey’s head was spinning from how generous Marge was. She picked out some sleepwear, slips, socks, tights and pantyhose as well.

“Lastly, we need to find you some shoes to wear.”

She had him remove his tennis shoes and measure his foot on the girl’s chart. They picked out a pair of black mary janes, a white pair of open toe dress heels and a pair of cute sneakers with a pretty pink streak.

“You are actually going to buy all of this stuff?” he asked looking at the large amount of clothing.

“Yep. I want you to have everything you need. I have a pretty nice bank account so don’t fret.”

“My my, some girl is getting very lucky today” the cashier stated as they checked out.

“Yes she is” Marge acknowledged giving Jeffrey the eye.

“I’d protest if I was you and demand some clothes as well.” The cashier joked as she looked at Jeffrey.

He smirked.
 
 
That day marked the beginning of Ashley. As soon as they got home Jeffrey ran into his room and unpacked all the clothing. He was like a kid in a candy store.

“Are you ever coming out of that room?” Marge asked a couple hours later as dinner was ready.

Jeffrey emerged wearing a pair of Pj’s they purchased. He was donned in the peach-colored short sleeved silky top and matching shorts. They were cute teenage girl pajamas.

“Well don’t you look cute Ashley.” Marge gushed. He looked awkward and unsure of himself. She could only guess at how nervous he was with all that was happening. She would do her best to make it seem like it was not such a big deal.

“Thanks” he replied feeling both uncomfortable and elated from her calling him Ashley.

They enjoyed dinner and finished the night by watching a movie.
 
 

The next morning Jeffrey was up early. He had trouble sleeping as he was very anxious about his first day as a girl.

His aunt was not up yet so he took the opportunity to make her some breakfast. He was elated that this huge weight had been lifted off his shoulders. He tried sending his parents signs of how unhappy he was but he feared that if they knew how he desired to be a girl they would disown him. Now though, he would be able to explore his fantasy of being a girl in secret with his aunt. Oh how he appreciated what she was doing for him!

He scrambled some eggs, made some pancakes and toast. He poured some orange juice and woke her up.

“What is this?”

“I made you breakfast! I hope you like it.” Jeffrey said with glee.

“This looks amazing Ashley! I didn’t know you were a cook.” She replied using his feminine name.

It struck Jeffrey again at how self satisfying it was to be called a girl’s name.

“So would you like me to do your makeup again today?”

“Yes!”

“Well, you seem to be excited about beginning you journey as a girl.”

“I am. It’s like a dream.”

Marge saw the incredible 180 Jeffrey had taken. He was a changed person since she let him explore his feminine side.
 
 
After breakfast was finished Marge asked Jeffrey to go get dressed and then she would apply his makeup. He went into his room and surveyed the assortment of clothes. He was so excited at the promise of this day. He wore the white button down blouse with puffed short sleeves for the top. He selected a short jeans skirt for the bottom. He loved the embroidered flowers on the back pockets.

He stepped into a pair of peach colored panties. They were cotton and fit snug against him. The feel was completely different from his boy underwear. They were so soft and delicate feeling and pretty stretchy. He admired the tiny elastic lace stitching around the waist and leg openings.

Next was the bra. He put his arms though the white garment and adjusted the straps to fit his torso. The cups kind of jutted out on their own. He placed the breast forms that his Aunt had purchased in them. He couldn’t believe all the money she must have spent on him.

The bra felt very foreign to him. He wondered how much he would like wearing it after the thrill wore off. It seemed a bit uncomfortable.

He put on the top which fit him like a tee and buttoned it up. He noticed how the buttons were on the opposite side than his boy’s shirts. He was getting a lot of butterflies in his stomach.

Jeffrey stepped into the opening of the skirt and pulled it up around his waist. He zipped up the back. It still felt so dang strange to not have anything separating his legs. There was just and open space in which he could feel his bare legs rubbing together…way weird!

He put on a pair of socks. How amazingly girly they were with lacy tops. Finally he buckled up his mary janes. He hoped that he looked ok as he walked into the family room. He felt uncomfortable with the clothes and despaired that he looked ridiculous. Taking a deep breath he entered the room.

“Well look at you girly! Looking good.” Marge said as she admired the pretty although incredible nervous looking boy. She would have to put him at ease.

“Shall we do your face up?”

“Ok” he replied trying to relax.

Marge applied his makeup all the while trying to calm his nerves. She told him about when she was his age and wanted to be a veterinarian. Her mother arranged for her to help out at a clinic near their house for the summer. She got to see ad participate in taking care of the animal first hand. It turned out that after that summer she didn’t desire to be a vet anymore but enjoyed the chance to explore that career. Marge compared that experience to Jeffrey trying life a girl for the summer. She stated that he may end the summer and find that being a girl wasn’t all he thought it would be. On the other though, she warned that he may love it and they would think of a plan if he did.

It was a great talk that left Jeffrey feeling very comfortable with him being a girl in front of her.

“There is one thing though. We need to shave those legs. Hair on a woman’s legs is so not ok.”

“Ok, other than that I look ok?” Jeffrey asked as he admired his made up face in the mirror.

“Yes sweetie, you are a doll.” She replied as she brushed his hair into a feminine style and clipped it with a white barrette.

“So now what?” Jeffrey asked.

“Just go about your day as normal. Pretty soon you will forget you are dressed like this and it will seem normal.”
 
 
So Jeffrey spent the day admiring himself a lot in the mirror. He couldn’t get over how this unreachable dream was actually happening. He was going to spend the whole summer as a girl! The butterflies where big in his stomach but he loved it. He did all the things he would normally do as a boy but everything seemed so much more pleasurable and alive with him as a girl. It was like the happy gates were opened up.

He even went into the back porch and drew a bit. Aunt Marge had rubbed off on him and he wanted to paint a nice picture for her. He spent a couple hours painting the large tree that was down the way. He admired his work. It looked pretty dang good!

Later that day he gave her the painting as a present which she adored. She couldn’t believe how joyful this boy was. Marge realized that this was something much bigger than Jeffrey could ever imagine. A boy relishing wearing girl’s clothes and having his makeup done was rare behavior. She knew it was only a matter of time before these issues would have to be addressed. For now though, she would let him have his time. He certainly deserved to be happy during his time spent with her. Heaven knows it had been a long time since he felt such happiness.
 
 
And so it continued. It had been a week since Jeffrey donned female clothes. He was basically living as a girl. He dared not leave the sanctuary of the loft and didn’t care to either. He was quite content being Ashley.

Marge was surprised at how well Jeffrey had adapted to living as a girl. He seemed very comfortable with himself now. All the fidgeting and anxiousness had quieted. He certainly seemed to be relishing this opportunity.

He had become more interested in art as well. This made Marge quite proud since she herself was an accomplished artist. He would go out on the patio and paint different scapes. They were actually very well done. He had a talent.
 
 
A knock came at the door.

“Hello” Marge stated as she opened the door.

A teenage girl stood at the entrance.

“Hi, I was wondering if the girl who lives here would like to come out and play.”

“The girl who lives here?” Marge asked. She wondered how anyone knew since Jeffrey wouldn’t venture outside.

“Yeah, I’ve seen her from our loft. She is outside on the patio painting all the time.”

“Ohhhh, could you hold on for a minute. Let me see if she is busy.”

She thought about if he was ready to be around others. It could be a great experience to help him figure out if this was right for him. Living in the confines of a house is a bit restricting and does not give the full picture. On the other hand, it could be disaster if someone found out he was not a girl.

“Ashley, we need to talk.”

“Sure. What’s up?”

“There is a cute girl at the front door who wants to know if the girl who lives here wants to play.”

“What?!? How does she know?”

“She saw you on the patio painting.”

“You told her to go away right?”

“Not yet. She’s waiting at the door. It might be good for you to get out of the house Ashley.”

“No way! What if she can tell I’m not a girl? That would be too much.”

“Honey, you will not have any problem passing as a girl. You may want to try it out. If you don’t like it then you won’t have to go out anymore.”

“I would be way too nervous. I don’t think I could do it.”

“You were nervous in front of me at first too and now look at you. If you really enjoy being a girl then you need to experience life in the outside world as a girl. Otherwise it’s just fantasy. Wouldn’t it be nice to see if you really do pass in the outside world too?”

“Well yeah it would…” Jeffrey replied hesitating.

“Then why don’t we invite her in. You don’t have to go outside and if things get weird I’ll step in and remedy the situation.”

“Ok I guess, do I look ok though?”

“You look beautiful. Just be yourself and you’ll be fine.”

“Do it now before I change my mind.” Jeffrey stated taking a big, deep breath.

“Sorry about that. Ashley has a little free time if you want to come in.”

“Sure!” the girl replied.

Jeffrey tried to hide his extreme nervousness. Would she be able to tell he was not a girl? Dressing in front of his aunt was one thing but in front of another girl who didn’t know? Would he fall flat on his face?

“Hi, I’m Lisa. I live right across from you in the next building.”

The girl wore jeans, tank top and sandals. She was very pretty he thought.

“I’m Ashley. Nice to meet you.” He replied trying to keep his voice soft and unwavering.

“I love your skirt! You got that at Macy’s right?”

He looked down at the skirt he wore. It was a light off white skirt that ended just above the knee. On the bottom of the skirt were embroidered light blue flowers.

“Yeah” he gulped just trying not to give himself away.

“I thought so. I wanted my mom to buy me that one but she said I had too many clothes already.”

Silence.

“So I haven’t seen you around here before.”

“I am spending the summer here with my aunt.”

“Oh ok, well I can show you around town if you want and introduce you to my friends. They are really cool.”

“That would be nice” He replied. She seemed to really think he was really a girl. He calmed himself more and tried relaxing.

“So what do you paint on your patio?”

“Here. I’ll show you.” Jeffrey said as he skipped to grab some of his paintings.

Marge looked on just in case she would have to jump in. She was concerned that Jeffrey was going to give himself away at first. The worst part was over though and he seemed to be adapting well.

“This is the tree that dips into out patio. This one is of the flower pot in the corner. This one is supposed to be of the sky and clouds but it doesn’t look very good.”

“I think they all look very good. I wish I was artistic like that. My art is dancing. I love to dance.”

“Cool! What kind of dancing?” Jeffrey asked. He felt more at ease with each passing sentence. Lisa thought he was a girl!
 
 
The next day Jeffrey got a call from Lisa who invited him to watch the new Harry Potter later on that day. He really wanted to see it but stepping foot outside the house seemed like such a risk. He declined.

“Think of it this way Jeffrey. When you look back on this experience will you regret spending all your time in the house?”

“Yeah, probably I will but what if someone catches on that I’m not a real girl? What do I do? I’m so freaked out about being embarrassed or even getting beat up.”

“Let me give you my perspective. I’m being honest here honey. You look like a teenage girl, you sound like a teenage girl and you carry yourself like a teenage girl. I wouldn’t let you leave the house if I knew that you could not pass but you pass amazingly well! Maybe you are not ready yet but you make a very pretty young lady.”

Those words were just what he wanted to hear. When he looked in the mirror he saw a pretty girl but he could also see the boy in him. He was so used to looking at a boy in the mirror that it was hard for him to see past that. Lisa seemed to really believe that he was just a regular girl…a girl that she actually wanted to hang out with! Could he summon up the courage to step foot into the real world as Ashley?

“I just need a plan if I get into a situation where I’m found out. What do I do?”

“I will drive you to the movies and pick you up. You have your cell phone on you and can call me any time. There are so many adults that will be around working. If anything makes you feel uncomfortable stay with an adult until I get there to pick you up.” She replied trying to set him at ease. She knew that he had to get out sometime soon.

“Oh man…I think I want to go.” He stated as he summoned up as much courage as he could.

“Well if you want to then give her a call back.”

He picked up his cell and hit the number. Taking a deep breath he waited for the rings.

“Hi Ashley, what’s up?”

“I changed my mind. I want to go tonight.”

“Oh cool! My mom is driving if you want to catch a ride.”

“It’s ok. I’ll meet you there”

They chatted about the time and meeting place and it was set. He was saying hello to the outside world.

“Ok Auntie Marge, what do I wear?” He asked with much trepidation.

“This is your big debut. What are you feeling? Jeans and a t-shirt? A dress?”

“I can’t wear jeans because they don’t look right down there.”

“Ohhh, I understand. I think that there are ways to hide that but it might not be a good idea to try it today. We don’t want you to be uncomfortable the whole movie.”

They headed to his room and she began shuffling through his clothes.

“How about this?” she asked holding up a lavender short sleeved dress.

“I really like that dress but it seems to fancy for a movie don’t you think?”

“You’re right. Oh, I’ve got the perfect outfit.” She replied as she pulled out the short denim skirt with flowers embroidered on the back side.

“This with this” She said as she showcased a pretty white short sleeved top. It was a snug fitting pullover.

“I think that would look really good.”

“It’s going to be a little chilly tonight so you should wear some tights or pantyhose to keep your legs warm.” She stated pulling out a pair of white opaque tights.

“Ok”

“Then your Mary-Janes would be a nice finish. Want to try it on and we’ll see?”

“Yep” he replied.
 
 
She let him be as he stripped down to his bra and panties. He smirked at the thought of how “normal” he was beginning to feel about wearing girl’s clothes. He found himself not even thinking about it for the most part. It had become just part of his life.
He sat down on the bed and bunch the white tights in his hand. With his toe pointed, he slipped his right foot into the bundle of nylon. He unraveled the silky material up to his knee keeping it taunt. Jeffrey repeated with his left foot. He stood up and began pulling the tights gingerly up each leg making sure that there weren’t any ripples. When he reached his crotch, he tugged lightly to ensure that the cotton gusset was snug between his legs. He finished pulling the control panty up and around his waist.

Looking down at the sheer, shiny nylon sent chills down his spine. Oh how he loved feeling pretty!

Jeffrey pulled the top over his head and down his torso. The cotton material clung to his body. He stepped into the jeans skirt, pulled it around his waist and zipped it up.

Buckling in his Mary-Janes, he stood up and looked in the mirror. He grew weak in the knees thinking about what he was about to do.

He met his aunt in the other room.

“You look gorgeous girl!” Marge gushed. He did look like a beautiful teenage girl.

“Let me just touch up your make-up a bit and do something with your hair.”

Marge went to work on him. The last couple days she had done his make-up very simply like a teenager would wear. Touching him up, she added a little more color to his eyes and a little shimmer to his lips.

“There ya go. Now those are some shimmery lips!”

He looked in the mirror fixated on the glossy, sparkly lips.

Marge focused on his hair. There was a lot of curling and teasing going on but the finished result was amazing.

“I think you’ll be happy with this.” Marge proudly stated giving Jeffrey the mirror.

“Oh my gosh…I love it!” He chirped. He ran to the full length mirror and took a closer look.

His hair looked like it had so much volume from the teasing. The wavy, gentle curls combined with the white headband took his feminine look to the next level.

“Oh Auntie, it looks so good!” he said with glee.

“I do have to admit that I’ve outdone myself.”

The two hugged and chatted like crazy until it was time to go. That’s right. The inward, quiet boy was now quite the chatterbox.

“Now remember I’m only a phone call away if you need anything. I’ll see you after the show. Don’t forget your purse.” Marge said as she dropped Jeffrey off at the outdoor mall where the theater was. Jeffrey stepped out the car and froze. All of a sudden it seemed as if the whole world was staring at him.

“Are you ok sweetie?” Marge asked.

“…Yeah.” He replied as he forced himself to take a step. He turned and waved her goodbye.

She drove off.

He was stuck now…trapped! The whole world was caving in on him…suffocating him. Deep breath Ashley! Deep breath! With clenched fists he began taking steps. Please don’t look at me! Please don’t look at me!
 
 
A group of girls passed by him and a couple of them smiled at him. He turned to see their reaction. There was nothing. They continued chatting. If they thought he was not a real girl they would have turned to look and probably giggle but they didn’t.

He took a few more steps attempting to control his racing heart.

Two boys were sitting on a bench. Oh crap! He looked down as he quickened his step to slip by them unnoticed.

“You look like you’re in a hurry…you late for a movie?” one of the boys asked.

Ok, be calm about this Jeffrey.

“Yeah, I’m meeting a friend here.”

“Boyfriend?” the boy asked.

He thought Jeffrey was a girl…or maybe he thought he was a gay dude in drag? Jeffrey’s mind was running rampant.

“No, she’s a girl...a friend of mine.” Jeffrey stammered trying to keep his cover.

“Well do you want me to be your boyfriend tonight?” The boy asked giving Jeffrey a wink.

“Umm, no thanks.” He quickly responded as he began walking again to get out the situation.

“Ouch! Dissed!” the other boy teased his friend.

Oh my gosh. They really did think they were talking to a girl! He passed!!! He closed his eyes for a moment and made up his mind to be at ease. He looked like a girl and he had to act like one to if this was going to work.

With a renewed vigor, he raised his head high and walked with confidence to the theater entrance.

“Over here Ashley!” Lisa shouted.

“Hi!” Jeffrey replied.

“Perfect timing. We just got here too. This is my friend Alicia. Alicia, Ashley. Ashley is visiting her Aunt here for the summer.”

“Nice to meet you” Alicia stated.

“You too. I love your necklace” Jeffrey replied trying to throw in a comment like he thought a girl would.

“Oh thanks! It’s my favorite one”

The three got in line to buy tickets and the conversation just flowed. Jeffrey grew more and more comfortable with his confidence.

They then lined up at the ticket window. Jeffrey instinctively reached into his back pocket to pull out his wallet. His hand brushed his backside before he realized that the pockets were only for show and girls don’t carry wallets. He quickly corrected himself and grabbed some money from his purse.

The three girls gave the ticket stubs to the elderly man at the entrance.

“You girls enjoy the movie. It’s the third on the left.”

“Thanks” Oh how he was on such an emotional high.
 
 
Waiting in line for refreshments, Jeffrey noticed just how many boys were looking at him. It was kind of freaky. Is this what girls had to go through? If he looked to the right, a boy would try to gain eye contact. The same thing happened when he looked left…and when he looked behind. He felt like his every move was being observed. He was being hunted or at least it felt that way.

The three got up to the counter and perused the various sweets.

“Can I help you out?” the geeky looking boy behind the counter asked. He was noticeably trying to act suave. It was plainly obvious to Jeffrey. How come he didn’t just act normal? Do all boys put up an act in the presence of women? Did he?

“Yes you can. What do you suggest?” Lisa asked in a playful, somewhat flirtatious way. Jeffrey wondered what the heck she was up to. She was way out of this boy’s league.

“Well…ummm…I like the raisinettes and the sour patch kids” He replied with a stutter in the presence of the pretty girls.

“Yummy! Do drinks come with that?” She asked biting her lip. Jeffrey knew that nothing at the movies was free. What was his friend thinking?

The boy blushed.

“What kind of drinks do you fine ladies want?” He replied with as much game as he could.

“I would like a diet Pepsi. Ashley, Alicia?”

“Seven Up for me please.” Alicia responded.

“A regular Pepsi for me” Jeffrey added.

“Coming right up!” he said as he prepared the three drinks and the candies.

“$5.25”, He stated as he leaned forward and quietly added, “The drinks and a box of jujubees are on me”

“Oh that is so sweet of you” Lisa replied with sincerity. She gave him a wink and a smile as they grabbed the items and headed for the theater.

“Do you know him?” Jeffrey asked.

“No way. He is so not my type, but he was nice to buy us stuff.” She replied while strutting her stuff like this happened all the time.

It dawned on his just how much power females have over men. Free candy and drinks just for a little flirting?!? That boy must have known that he was getting played but he did it anyways. Was it worth losing his job over just to chat with a pretty girl even for a few moments?
The girls chatted like crazy before the film began. They talked a lot about boys and clothes. Jeffrey stayed quiet and closely observed. After a couple minutes he began joining in the conversation and fit in nicely.
 
 
Even as the movie played, he found himself just plain giddy. The three giggled like, well…like teenage girls do. It was so freeing to just be as silly and “girly” as he wanted to and no one thought any less of him. He never realized that girls talked about boys the same way that boys talk about girls.

“Don’t you think Harry is gorgeous Ashley?” Alicia asked expressing her crush on the wizard.

“Yeah” he replied trying to think of what a girl would say, “I wish I could use that love potion on him”

“Oh I like you girl…great taste!”

Jeffrey looked down at himself during the film. Here he was sitting in a public movie theater dressed completely as a girl. Not once single article of boy’s clothing on him. It was nerve-wracking yet thrilling all at the same time. He was walking a fine line. To the outside world he looked completely normal. Completely normal since everyone’s perception was that he was a regular teenage girl. How drastically that would change though if the only knew that he was not a girl. All these people who see nothing wrong with him would suddenly change their perspective 180 degrees. He would become a strange, abnormal, weird boy who wants to be a girl. Lisa and Alicia would probably laugh their heads off at his expense. He was a “normal” girl right now but one false move and he would become a sissy…a fag…a pervert.

He developed a bad taste in his mouth. Don’t think about those things! Relax and you’ll be fine. He put the negative thoughts away and focused on the movie once again.
About halfway through the movie Jeffrey began feeling pressure on his bladder. Why did he gulp down his drink like that? He would have to hold it.

As the movie continued he began feeling unbearably uncomfortable and the movie had no end in sight!

His urge took over and he excused himself. As he walked out of the theater he saw that the hallway was packed. Another movie must have just let out. Obviously he would have to use the girl’s restroom and tentatively walked to that door. The universal symbol of the women’s room was displayed on the door. A woman wearing a dress…that was him. With a shaking hand, he grabbed the handle and opened the door. He walked in actually feeling grateful that he had to go pee so badly or else he would have been to scared to go in there. He was sure that he would get arrested if someone found out that he was a boy in the girl’s bathroom. That’s illegal isn’t it?

As he entered the bathroom he quickly found that he was the fourth in line. He would have to relax and pretend like he was used to being in there even though he had never stepped foot into a women’s restroom. All stalls…a feminine shade of pink and purple…the tampon machine…the soft smell…the way the girl’s primped and adjusted their makeup. He took it all in.
 
 
Finally it was his turn. He had practiced this at home and he would have to duplicate it here. He closed the stall door, pulled the seat protector and laid it down. He turned his back to the toilet and lifted his skirt. He could hear the woman in either stall next to his…he was in the women’s restroom!!! He pulled his tights and panties down to his knees and sat on the toilet. He focused on making the same sound as the other women were making with his stream. He even rolled a little toilet paper after he was finished.

Jeffrey pulled his panties up followed by his tights. He made sure that there wasn’t any laddering. After pulling down his skirt he opened the door and looked around to see if his cover had been blown for any reason. One woman smiled at him as if there was nothing amiss. His confidence grew. He went to the sink and washed his hands. Looking in the mirror he now saw a girl. He looked really good and he knew it. As he left the restroom and headed back into the theater he felt like he was floating on air.

What a great movie!

The three girls finished the movie. Jeffrey couldn’t remember how long it had been when he had enjoyed a movie so much. He felt electric the whole time.

“So do you have to go home or do you want to hang out?” Lisa asked Jeffrey.

He was on such an emotional high at the moment and was filled with a new sense of confidence that he looked like a girl, he sounded like a girl…and for all intensive purposes he was a girl.

“Let me call my Aunt.” He said as he quickly dialed Marge’s phone.

“How was the movie? Did everything go ok?” Marge asked.

“It was such a good movie. Yeah, we had a really good time Auntie!” Jeffrey replied with glee.

“Wonderful! I told you that it would be fine. I’m on my way. Just give my about 10 minutes.” She stated.

“Ummm, do you think I could hang out for a while with Lisa and Alicia?”

“Oh you feel comfortable enough? That’s exciting news.”

“Yes, I feel really at ease right now.”

“Ok sweetie, call me if you need anything at all. I’d like to pick you up in a couple hours alright?”

“Ok Auntie. Bye”

“Alright, I have a couple hours.” He told the other two girls.

“Goody!”

The three girls entered the mall. Alicia and Lisa knew this turf well. Jeffrey got the feeling that they spent many hours there.

“Okay, possibly the most important thing you need to do since you are new to this town is get familiar with the shopping establishments.” Lisa joked.

They took Jeffrey into all of the hip stores showing their new friend the ropes. Although still on nerve because he didn’t want to blow his cover with a slip up, Jeffrey was growing more and more confident that this was something he could do. He was feeling very free to be “himself” without fear of how girly he acted. There weren’t any “masculine” lines that he would have to abide to. He was relishing the fact that he could wiggle his hips, sashay his walk, sway his hands without fear.

“Oh this skirt would look so cute on you girl” Lisa stated at one store as she held up the plaid mini skirt up to Jeffrey’s waist. He looked down and agreed.

“Did your Aunt give you her credit card?” she asked Jeffrey.

“Nope, I should ask for next time though.”

“Definitely! You can’t go to the mall without any money silly. That is unless you have a rich boyfriend.” Alicia joked.

The next stop was the Mac makeup store.
 
 
“What kind of eyeliner do you use Ashley? I need to get me some. Your makeup always looks so flawless.” Lisa asked.

“Ummm, it’s…a…I’m not sure.” He stuttered. Please don’t mess this up Jeffrey!

“You don’t know?!?”

“Well, my Aunt has been doing my makeup for the last few days. I…uhh…left my makeup bag at my parent’s house and they haven’t mailed it yet.” He grasped for an excuse.

“Oh wow, I would die if I didn’t have my makeup case.” Lisa replied “so your Aunt does your makeup everyday?”

“Yeah, she really likes doing it.”

“You so have to get her to do mine and Alicia’s! She is way awesome at it!”

“I’ll ask her. I’m sure she would…she’s totally into it.” He answered hopefully off the hook.

Alicia knew the girl at the Mac counter and introduced Jeffrey.

“You have great bone structure and I would kill for those lips.” The makeup girl complimented him.

“Thanks!” he replied calming himself down.

The three looked at different makeup, nail polish and perfumes. They even sprayed Jeffrey with the new scent by Britney Spears. He really liked its scent.

“Wipe off your lipstick. I think this color would look fabulous on you.” The makeup artist asked Jeffrey.

“You’ll want to listen to her, she is amazing” Alicia added.

He grabbed the moist towelette and wiped the lipstick off.

“Try this one on.” The girl told him as she handed over the shimmery deep red lipstick.

He froze. He had practiced putting on lipstick but was not very good at it. He always seemed to go outside the lip lines. He would look like a total amateur in front of his friends.

“Ummm, could you put it on me? You are the pro.” He answered in a somewhat joking tone.

“Sure!” she replied grabbing her lipstick brush.

She ran the brush over the lipstick and gently applied it to his lips. He really couldn’t believe that this was happening. In all his dreams he never thought that he would actually be in this position.

“There ya go. Take a look and tell me if I’m right.”

He looked in the mirror and was very pleased with the results. His lips were a deep red that was offset by tiny little shimmery sparkles.

“I told you she was magic” Alicia said

“Thanks so much. I’m coming back to buy that one.” He replied.

Another thing that struck Jeffrey was just how much attention was directed his way from boys. Girl’s hardly ever even made eye contact with him as a boy, but as a girl he felt like he was the center of attention. Boys were not even discreet. They would stare him up and down and they turn their heads as he walked by. Some even added comments. Oh what a difference

Marge picked Jeffrey up.

“So I take it that you had a good time Ashley?”

“Oh my gosh Auntie, we had so much fun! The movie was great! After that we walked around the mall and Lisa and Alicia showed me all the cool stores. They are awesome! They spend a lot of time there Auntie and know so many people that work there. I never knew the mall was so cool before. I mean, it’s just a fun place to hang out and people watch. Alicia bought me a cinnabun and we just hung out in the food court and chatted forever. I want to earn some money so I can actually buy stuff there.”

“Whoa take a breath there sweetie. I’m so glad you enjoyed yourself. I like that lip color on you.”

“That’s another thing. Alicia has a friend who works at Mac and she knows so much about make-up. I told her about you and how talented you are also. Speaking of that, Lisa wants you to show her some makeup tips because she loves how you do my makeup. Anyways, her friend looked at me and said that I would look really good with this lip color and put it on me. I really like it and told her I would be back to buy it when I get some cash.”

Marge was awestruck at the rambling Jeffrey. His mouth was running non-stop just like a teenage girl’s. This wasn’t just a curiosity was it? The more she thought about it the more she began to realize that there was something very amiss with Jeffrey. His transformation not only physically but emotionally was amazing.

“Well good honey. So you didn’t have any problems with anything?”

“None Auntie. I almost forgot that I was dressed like this. After a while I just felt really comfortable.”

“So I take it you would like to go outside again as Ashley?”

“Yes!”
 
 
As they arrived, Jeffrey headed to his room to call his parents. His mother insisted he call every night. He felt very at ease talking to them even thought he didn’t let them know that he was experimenting with being a girl. He trusted his aunt and her promise that she would not tell them.

“Hi mom”

“Hello baby, how are you doing? Having a good time?” his mom answered. She was hopeful that Marge was turning her son around. The last few phone calls found him in a better mood and a happier demeanor.

“I’m having so much fun mom. Aunt Marge is by far my favorite aunt. I’ve met some friends and they are very cool.”

“Well that’s very good news. I can hear in your voice that you are having a blast. That makes me so happy Jeffrey. So you have made new friends?”

“Yep. We went to the movies today and then just hung out in the mall for a couple hours.”

“Great!” his mom replied. This decision to let him get away for a while was just what he needed. “So you don’t want to come back home early?” she joked.

“No mom, I really like it here. I miss you guys a lot but it’s so much fun being here.”

“Well we miss you so very much also but I think this was such a good opportunity for you.”

“It is mom.”
 
 
The two chatted for another few minutes before saying goodbye. He knew that if his parents knew what he was doing here they would be furious. He would just enjoy his time here while he could and then deal with the rest later.

And so Jeffrey went another week as Ashley. Marge knew that she would have to have a serious talk with him sometime soon. As the time wet on she realized that this wasn’t just some fetish or phase that he was going through. For all intensive purposes he was a girl. It had been three weeks since she let him dress up and he had not looked back. 24/7 as a girl since that day. This was not normal behavior by an means.

Jeffrey on the other hand had grown very comfortable with being Ashley. Getting up in the morning, putting on his makeup and slipping into a dress or skirt were normal to him now. The newness had worn off and the insecurities had diminished.

Alicia had invited him over to her house for a BBQ. It was her grandmother’s birthday and she wanted Ashley to be there so that she wouldn’t be bored. Too bad Lisa couldn’t come also but she had other plans.

Jeffrey sat by his makeshift vanity and applied his makeup. Aunt Marge showed him the basics and he had become pretty good. He always showed her after he was finished to get her opinion. He went light with a little powder, tan eye shadow and shimmery lip gloss. Jeffrey finally decided upon a yellow sundress. It was adorable with semi-thin shoulder straps, a white flower print and touch of white chiffon that poked out from the bottom of the skirt. He matched it with some yellow sandals. Should he have changed his nails polish?

“Auntie, do you this nail polish looks ok with the outfit?” he asked. His toenails and fingernails were painted a light pink.

“That looks fine sweetie. You are wearing soft colors. Pink and yellow go well together. Your make-up looks pretty also.”

“Thanks! Can you do something with my hair?”

Marge complied and French braided his hair tying it with a yellow ribbon.

“There ya go princess.”

Jeffrey looked adorable. His mannerisms were so soft and feminine now. He even sat like a lady when she braided his hair with his legs and feet gently crossed.

“Hey girl!” Alicia said giving her friend a hug. I’m glad you’re here to keep me company.”

“Nice house.” Jeffrey replied. She had a huge house. No wonder she could afford all those clothes and stuff.

“Let’s go in the backyard and I’ll introduce you to everyone.”

Alicia took him to say hello to her grandma first. Grandma commented how much she loved Jeffrey’s dress.

“Oh how nice it is to be pretty and young” she stated.

“This is my sister Meghan. She’s the drama queen of the family.”

“Yeah, I learned it all from you sis.” Meghan joked

“It’s nice to meet you Meghan.” Jeffrey said. She looked a lot like her older sister.

“You too. My brother is going to like you.” Meghan added.

“He probably will Ashley, but he’s cool. I have to warn you though that he is quite the charmer.”

Jeffrey didn’t know what to think about that.

“Hello ladies” a voice came from behind.

“Oh hey bro, we were looking for ya. I want to introduce you to my friend Ashley.”

“Hey Ashley, I’m Scott.”

“Nice to meet you Scott.”

“You didn’t tell me you had such a pretty friend sis.” He somewhat joked with Alicia. This girl was just plain hot.

Jeffrey found himself blushing over Scott’s compliment. Blushing?!? He gained his composure.

“Nice to meet you Scott”

Scott looked the kind of guy that Jeffrey despised in school. He must have been popular…he just seemed the type. He figured Scott as a jock who dated cheerleaders and picked on guys like himself.

“Mind if I hang out with you girls?” he asked leaning in close, “this is a pretty boring party”

“That’s why I invited my friend Einstein. You should have invited a buddy as well” Alicia replied.

“Oh come on. I promise I’ll behave.” He pleaded hoping to hang with his sister’s pretty friend.

“Do you mind Ashley? He does have his good points I guess” Alicia asked.

“It’s ok with me” Jeffrey replied. He wasn’t sure how he would act in the presence of a boy or how a boy would treat him. Good thing he felt very comfortable with himself as Ashley.
 
 
So the three chilled on the patio for a while and enjoyed some lemonade and chips. Jeffrey had his guard up with Scott. He wasn’t sure what to expect.

“So where are you from Ashley?” he asked. He admired the way her sundress cascaded off her smooth legs. He noticed how her toenails were so prettily painted. He loved a girl who took care of herself.

“Riverside County”

“Cool. So what are you doing here?”

“I’m visiting my Aunt for the summer. She invited me and I really like her so I said yes.”

“So do you have any brothers or sisters?”

“Yeah. I have a brother and three sisters.”

“Dang, so your brother has to deal with four sisters. Life must be rough” he joked.

That statement sent chills down Jeffrey’s spine. He was the other sister wasn’t he. His older brother was the only male wasn’t he?

“He doesn’t complain.”

“I see your point. It could be nice to have all of his sister’s friends over.”

“uh yeah.”

“Oh come on, I was just joking. So are you having fun so far?”

“Yep. I’m having a great time.”

Scott found himself smitten with his sister’s friend.
 
 
The three had a little lunch and enjoyed each other’s conversation. Jeffrey kept a close eye on Scott. He seemed a likeable guy but hanging with a boy was just too weird. Being around Lisa and Alicia was one thing. It seemed harmless. Being around a boy knowing what boys think made him very uncomfortable. The BBQ ended as Jeffrey said goodbye to everyone. Alicia’s grandma was a nice lady.

“What no goodbye? I thought we were beyond that?” Scott stated as he noticed that his sister and Jeffrey were leaving.

“Oh sorry, I’ll see you later.” Jeffrey replied. He was hoping he could get out of there without notice.

“It was nice getting to know you Ashley. Maybe I could show you around town sometime.”

“Yeah, maybe.”

“Hey, don’t be flirting with my friend ok?” Alicia stepped in. She noticed how Jeffrey was squirming.

“Okay okay. Later girls.” He replied as he dropped his come on.

“Sorry about my brother. He really is harmless.”

“It’s alright.” Jeffrey answered.
 
 
That night Jeffrey told his Aunt all about his day. He even confided to her how he felt Scott was paying so much attention to him.

“Well sweetie, you can’t get upset at him for showing interest. Physically you look like a pretty teenage girl and his hormones are on overdrive.”

“So should I stay away from him?”

“It’s up to you. Can I ask you a personal question honey?”

“Sure”

“Are you attracted to boys?”

“What?!? I can’t believe you asked that? No, I don’t like boys.”

“Sorry, it was just a question.” Marge replied in a very apologetic tone.

Is that what she thought of him? Oh my gosh, why wouldn’t she think that? He was living as a girl so why wouldn’t she think he was gay? Regular boys don’t do this…but he liked girls.

“It’s ok, I know how you could think that but I don’t like boys that way.”

“So it’s up to you. If you hang out with this boy then just be aware that he is going to treat you like a girl and be attracted to you as a boy would a girl”

“Well what do I do if he tries putting the moves on?” Jeffrey joked.

“Oh it’s easy to control a boy. The woman has all the power. If he gets out of line just walk away”

Jeffrey and his Aunt had a great conversation filled with laughs and memories of her as a teenager.
 
 
The next day Jeffrey got a phone call from Scott.

"Hey Ashley, I was wondering if you wanted to hang out today? There’s a carnival downtown that looks like a lot of fun.”

Jeffrey really didn’t care to spend the day with Scott. It made him nervous to hang out with a boy. Acting girly around girls was easy for him but doing the same while around a boy concerned him.

“I don’t know Scott. I need to see if my Aunt already had plans.”

“Alright well if you want to go and it’s ok with your Aunt then give me a ring. I am going to be leaving here in a couple hours. I promise you’ll have a great time if you decide to go.”

Scott did sound convincing and a carnival sounded like a blast. Could he pull of being a girl in front of a boy though? What if Scott found out and beat him up? That wouldn’t be good.

“Let me give you a call back ok?” Jeffrey asked Scott.

“Ok, I’ll be waiting patiently by the phone.” He joked which made Jeffrey giggle.

Jeffrey consulted his Aunt about what to do. She was on the same wavelength that he was used to. She encouraged him to confront his fears but to be safe about it. A carnival was a relatively safe place with multitudes of people around. She then suggested that Jeffrey call Alicia to get her opinion of him hanging with Scott.

“So your brother just called and asked if I wanted to hang out with him today.” Jeffrey notified Alicia.

“I thought he might. By the way he thinks you’re beautiful.”

“What do you think I should do?”

“It’s up to you I guess. Scott is way cool and you would have lots of fun. He’s is a very decent guy too so don’t worry about feeling uncomfortable.”

So he was given the green light by Scott’s sister. With a truckload of courage he picked up the phone and called Scott back.

“Ok Scott, I can go to the carnival”

“Alright! I can’t wait! Can you be over here in about an hour?”

“Yep”

“What should I wear Aunt Marge?” Jeffrey asked.

“Well I would suggest tennis shoes for sure if you are going to be on your feet all day. Shorts or pants might be better than a skirt for this occasion” Marge suggested.

“I don’t like wearing shorts or pants because you can see a bulge down there. It’s not flat like a girl.” He replied. It was true. Whenever he tried on the cute shorts his aunt bought him they never look right. Therefore he always stuck to skirts or dresses.

“I see what you mean. Well wear a skirt then. If you wear leggings or tights under it and you’ll be fine.”
 
 
Jeffrey settled on a short black denim skirt which was lightly frayed at the bottom. He paired it with a pair of black opaque tights, and a white ___ t-shirt that fit him like a glove. He opted for a pair of black tennis shoes. The look of the outfit was very feminine yet very hip.
He walked out and modeled for Marge.

“What a doll! I have a great idea for your hair." She parted his hair down the middle and French braided it on both ends forming pigtails. She secured them with beaded rubber bands.

“That looks so cute Auntie!” Jeffrey gushed.

“I think I’m ready”

“Well you look adorable. Be careful and call me if anything worries you.”

They hugged and Jeffrey headed to Scott’s house.

“Hey, good to see you again!” Scott said.

“You too” Jeffrey replied as they gave a small hug to each other.

“Here’s your bike. Ready?”

“My bike? You didn’t say we were riding a bike.”

“Sorry I didn’t mention that. Crap, you’re wearing a skirt too. I’m sorry Ashley. You can’t ride a bike in a skirt can you?”

“I don’t think so”

“Let me see if my mom can drive us then.”

Scott came out a minute later with his mother.

“Nice to see you again Ashley. Oh dear Scotty, you wanted her to ride a bike wearing that? I’m sorry Ashley, boys just don’t understand sometimes do they?”

“It’s ok Mrs. Anderson.”

“Alrighty hop on in kids” Scott’s mother asked.

Scott quickly went for the front passenger side door.

“Scotty! You should offer to let Ashley sit up front. We have to talk about the proper way to treat a lady my boy.” His mother jokingly scolded him.

“Sorry…err, why don’t you sit in front Ashley.” He stumbled.

“Ok!” Jeffrey replied as he hoped in the front seat. He wasn’t used to being put on a pedestal. It was pretty nice.

Scott’s mom dropped them off at the carnival. It looked really cool with several big rides and lots of games. Scott took the liberty of paying for both of them which seemed really foreign to Jeffrey. He tried to pay his own way in and expressed that to Scott who would not have any of that. He insisted that he was paying.

“Shall we play some games or do you want to go on some rides?” Scott asked.

“I want to play some games” Jeffrey replied.
 
 
The two headed over to the carnival games. Jeffrey was never the most athletic type so he figured he could just be himself. He felt electric about being out with a boy as Ashley. The fact that he could act as feminine as he wanted and Scott wouldn’t look down on him made him smile. He felt so free.

“Basketball toss? I’m awesome at this game.” Scott stated as he urged the pretty girl to choose that game.

“Sure!”

Scott paid for both him and Jeffrey to play. Once again Jeffrey objected to Scott paying but it didn’t matter.

“Give it up Ashley. This whole day is on me. I’m serious…I want to pay for everything.” Scott let Jeffrey know.

So this is what it felt like for a girl to be out with a boy. Jeffrey liked it although it felt odd. Females were spoiled! Scott let Jeffrey go first. Having a great time being as girly as he wanted, Jeffrey decided to throw the ball “granny” style. He grasped the basketball and scooped it underarm missing the basket completely the first time.

“Come on girl, you can do better than that. Just a little more force and you’ll get it in” he encouraged her. He thought it was cute how she tossed the ball like that.
The second ball bounced off the rim and the third did likewise.

“Nice try Ashley. Let me see if I can win something.” Scott stated as he focused on the basket in an attempt to really impress Jeffrey.

Jeffrey was loving life. He just made three very pathetic attempts at making a basket. As a boy he would have been ridiculed and embarrassed especially at the way he tossed the basketball underarm. As Ashley though it was fine and Scott made him feel like he did a great job even though he didn’t make a single shot. Being a girl was magical.

Swoosh! Scott made the first basket.

“Good Job!” Jeffrey yelled.

Scott grinned as his ego was pumped. He shot another with banked and dropped into the basket.

“That’s two! I told you I was good at this game” Scott gushed.

“Let’s see you make the last one” Jeffrey replied.

Scott focused on the task at hand and let the ball flow off his fingers. The ball arched high and settled right in the middle of the basket. Another swish!

“Alright!” Scott yelled.

“Good job! You showed me up.”

“So you get a big stuffed animal. What’ll it be?” the carnival guy asked.

“You pick one out Ashley.” Scott directed.

“You won the game. Why don’t you choose which one you want?” Jeffrey replied.

“I like playing the games but I’m not into stuffed animals so go ahead and pick what you like.”

“Alrighty then” Jeffrey replied as he looked over the array of stuffed animals, “I’ll take the purple rabbit.”

“A purple rabbit?” Scott replied as the vendor handed Jeffrey the animal, “there’s no such thing as a purple rabbit is there” he joked.

“I don’t know but I think it’s cute.” Jeffrey stated relishing how girly he found himself acting.

“Well if it makes you happy then mission accomplished!” Scott smiled.

Jeffrey hugged the purple stuffed animal in the most girly way he could wrapping his arms around it and swaying it back and forth. He was letting himself get totally engulfed in his feminine feelings and kept an eye on Scott to see his reaction.

Scott just smiled as if Jeffrey’s behavior was normal…for a girl.
 
 
They played a few more carnival games and Jeffrey let himself play the girl part to the extreme. He intentionally acted like he didn’t know how to throw a dart at the balloons. He flayed “like a girl” at the milk bottles. How he was enjoying himself!

“Well you certainly are a pro at these games Scott” Jeffrey complimented, “What am I going to do with all the prizes though?” he asked looking at the pink lizard, the rainbow care bear and the bratz babygirl doll.

“Let’s drop them off at out locker and hit some rides” Scott suggested.

After losing the toys, they headed over to the rides choosing the Ferris wheel first. Jeffrey couldn’t remember the last time he had such fun. He didn’t realize that boys could be so nice and gentle. He was used to the raunchy, rough-housing behavior that boys displayed towards him usually. It was amazing how much different they acted around girls…like night and day.

They rode up the wheel and enjoyed the beautiful view. Jeffrey felt a little uncomfortable sitting close to Scott in a confined box but kept his calm. He was sure that Scott was attracted to him but Jeffrey wanted nothing like that from Scott.

Scott was so much fun though! He was funny and made Jeffrey laugh so hard on the Ferris wheel. Oh Scott was so cool and amazing!
 
 
After the wheel they decided to spice things up with a ride on the roller coaster. It wasn;t a huge coaster but it looked scary nonetheless.

“You scared Ashley?” Scott joked as they were buckled into the seats.

Jeffrey wasn’t scared but thought it might be fun to act the part.

“Yes…I’m a big scardy cat.” He replied with a pouty lip.

“Oh, it’ll be ok. If you get scared just close your eyes and it’ll be over before you know it.” Scott stated. He thought it was adorable how she was so frightened.

The ride started and Jeffrey let himself scream like a girl at the top of his lungs. He was having a blast!

Scott cracked up as well at how the pretty girl lost it.

“That was pretty dramatic don’t you think Ashley?” Scott joked afterwards.

“Ok, so I overdid the screaming a bit” Jeffrey came back at him.
 
 
Next up was the Merry Go Round. Jeffrey had loved that ride since he was a little boy. They hoped on the platform and walked together to find which animal to ride. Scott jumped on the black stallion with the ruby saddle while Jeffrey opted for the white unicorn with the pink rhinestone saddle.

As he put his foot in the holster to straddle the horse he realized that he was wearing a skirt. Damn! He became so comfortable with himself that he forgot that he was wearing the mini. He wouldn’t be a able to straddle the unicorn. His skirt would ride up and the world would be able to see under it. How was he going to ride?
“Go ahead a get on the horse dear” the female ride attendant asked.

Jeffrey stumbled on his words not knowing how to approach this ‘new” situation for him. He didn’t have the experience of a regular girl to fall back on.
The ride attendant picked up on his dilemma whispering in his ear, “Put your right foot in the holster, keep both legs on this side and side-saddle the unicorn” she instructed as she helped Jeffrey mount the horse.

“Thank you” Jeffrey said in an embarrassed red glow.

“Being a girl has its challenges at time doesn’t it?” Scott joked giving Jeffrey a hard time.

“Be quiet!” Jeffrey replied acting very dramatic in a fun way, “You try wearing a skirt”

“You wouldn’t want to see me in skirt. You look much better in one than I” he stated in a flirty way.

Jeffrey blushed once again. Even though he wasn’t into boys he oddly found himself loving the compliment. They had a wonderful time going round and round. Jeffrey felt a little off balance at first but quickly became comfortable with riding the horse side straddle.
 
 
After the Merry Go Round, they headed over to the food court to grab a bite to eat.

“I’m having such a great time Scott” Jeffrey blurted out. He just had to tell him since this was the finest day of his life thus far. He was spending the day at a fun place with a cool guy…as Ashley!

“Thanks! So am I. I think you are an awesome girl and I like hanging with you” he replied. He was very attracted to Jeffrey but knew he would have to take it slow.
 
 
After lunch they played a couple more games and rode a ride or two more before it was time for Scott’s mom to pick them up.

“Wow! You two made out like bandits.” Scotts mom said as she saw them carrying out a few prizes.

“Scott won them all but he was nice enough to let me pick what I wanted.” Jeffrey stated as he hoped into the front seat. Scott’s mom met him on the driver’s side.

“Good job on letting her pick the prizes. That’s the way you score points Scotty.” She complimented him as they opened the doors and got in.

Scott’s mom pulled into Jeffrey’s driveway.

“I’ll see you later Ashley. Why don’t you carry her prizes into the house for her Scotty” his mom advised him. She was always trying to teach her sons how to properly treat a lady.

“Ok mom.” He replied grabbing all the prizes.

They dropped the stuff inside.

“Well I had an awesome time Ashley. We should hang out again soon.” He stated hoping that she had as good a time as he did.

“It was so much fun today Scott. I would love to hang out again.” Jeffrey replied. Did he just say that he would “love” to hang out with a boy again?

“Nice! Well….ok….see ya later.” Scott nervously replied as he headed out to the car.

“Bye bye” Jeffrey waved. He thought it was kind of cute how nervous Scott became. He actually made a boy nervous? Once again, it was weird but pretty cool.

“Well look at you sweetie. You had a fantastic time didn’t you?” Marge asked looking at all the stuff. She was becoming more concerned at his “Ashley time”. He was Ashley twenty four hours a day — seven days a week. This was obviously not a passing fad and his issues would have to be addressed soon. He just looked so happy and at peace with himself that she had a hard time raining on his parade.

“Yes I did! Scott won all this stuff for me.” Jeffrey gushed as he explained for several minutes how good Scott was at all the games.

Marge wondered about the way that Jeffrey was talking about Scott. It surprisingly sounded a lot like how a girl speaks about a boy she has a crush on. Could he be gay as well?

“Honey, sit down”

“Ok”

“How do you feel about hanging out with Scott?”

“It’s amazing. He’s a really cool guy.”

“Is it like hanging out with your best ‘guy’ friend back home?” she tried digging further.

“It’s way better. Scott treats me a lot better than any of my guy friends back home.”

“He treats you that way because he thinks you are a girl. You know that right?”

“Of course I do. I’m just saying that he’s really sweet I guess.”

“Do you have a desire to be more that just friends with him?”

“What? Oh no…I know what you’re thinking and you are way off base. I’m not attracted to him like that.” Jeffrey replied trying to drive his point home.

“Ok. I was just checking is all. He’s just a cool guy then?” Marge replied not really sure if she believed him.

“That’s it. He’s just a cool guy to hang with.”
 
 
The next hour and a half was spent with Jeffrey going over every detail of the fun filled day. He sure loved to talk. Marge let go of all her worries concerning the gender confusion in her nephew and just enjoyed chatting with the young woman.

Later that night Alicia called Jeffrey.

“So Scott hasn’t stopped talking about how much he liked going to the carnival with you today.”

“Really? What did he say?” Jeffrey replied with curiosity. He wanted desperately to know what Scott really felt about the day. Why was he so concerned over if Scott had a good time?

“He said that this was the best day of summer so far. Between you and me Ashley, he really likes you...alot” Alicia answered.
Jeffrey felt a warm butterfly sensation inside. He had never had this feeling before and was unsure of what it meant. Why did Scott liking him make him so dang happy?

“Oh cool. He is so much fun Alicia."

The two spent about a half hour chatting the way girls do. Alicia giggled as Jeffrey kept finding a way to bring every topic back to her brother.

"So did you talk to Ashley yet?" Scott asked his sister later that day.

"Yep and she is way into you Scotty. You are quite the ladies man aren't ya?"

"Ahem" Scott replied as he jokingly gave himself a pat on the back.
 
 
The next day Scott called Jeffrey and let him know about how his friends were going out the next night. They were going to go out to eat somewhere, watch a movie and then head to his cousin’s house to chill.

“Alicia and her boyfriend are going too so I was wondering if you maybe wanted to go with me?” Scott asked keeping his fingers crossed.

“I would really like that.” Jeffrey quickly responded with glee.

“Awesome! So I will pick you at around 5pm?”

“I’ll be ready”

As soon as he got off the phone with Scott he called Lisa. It turns out that Lisa was going as well.

“It’ll be a lot of fun Ashley. We have a ‘date night’ every couple weeks with bunch of us.”

“I can’t wait”

“Oh Ashley, I was meaning to ask you if I could borrow your flower print skirt? I have been looking for a reason to wear it since I met you” Lisa asked.

“Sure, you can burrow whatever you want.”

“So you’re going with Scott huh? Is there something going on between you two?” Lisa hinted.

“No…we are just friends. He’s a cool guy” Jeffrey responded keeping her questions at bay. Why did everyone assume that they had a thing going?

“So what are you going to wear?”

“I don’t know. Do you dress up for this?”

“I like to. You know what? I have a dress that would look so cute on you Ashley. I’ll bring it tomorrow. Do you want to get ready together? Maybe your Aunt could do my makeup.”

What a question! Get ready together? With a girl? He loved the idea but and the risk was very low if he changed in the bathroom.

“Sure, come over early. I’m sure Marge would love to help you.”

“Sweet!”

Jeffrey told his aunt about the plans for the next day and that Lisa would be coming over to get ready. Marge was in a bit of a sticky situation now as Jeffrey’s love for being Ashley continually grew. Nonetheless she said it was fine all the way around.
 
 
The next afternoon Lisa arrived with a bag full of stuff.

The two went into Jeffrey’s room and Lisa pulled out the dress.

“Here it is. Isn’t it gorgeous? I also brought the heels to match.”

It was stunning. It was a light blue baby doll style dress with medium sized straps that did a fancy cross-over at the breast area. There was a white ribbon that tied high up on the waist that fit the dress’s style. The skirt was several layers of very fine chiffon that flowed to just above the knee.

“Oh Lisa, that dress is amazing!”

“So you want to wear it tonight?”

“Yes, thank you”

The two girls went out and visited Aunt Marge and took turns letting her do their make-up. They giggled and chatted like teenage girls do. Jeffrey loved what she did with Lisa face.

“I’m going to give you an evening look too Ashley” Marge stated as she gave his eyes a little more smokiness and his lips a deeper red.

“Ok girls, my work it done.” Marge stated as she finished up.

She was looking at two young women. Was it a birth defect or just something that went wrong? Whatever it was, she was convinced that Jeffrey really felt like himself when he was Ashley. How was she going to handle this with his parents?

“Let’s go get dolled up girl” Lisa said as she grabbed Jeffrey’s hand and led him into his room.

“Let me do your hair. You will love it” Lisa prompted Jeffrey. He agreed and sat still as she put his hair in curler, then gently brush his tresses in a beautiful, flowing, curly mane.

“You are amazing Lisa” Jeffrey stated as he adored his reflection in the mirror. There was a very pretty girl staring back at him.

He gave Lisa his skirt and a tight fitting top out of his closet. She was so excited as she had coveted that skirt for a while now. Lisa proceeded to remove her jeans right in front of Jeffrey. His eyes bugged out. He had a girl in his room stripped down to her panties! He began to perspire as she removed her top as well. There she was wearing nothing but her pretty bra and boy short panties.

“Ashley, you face is all red. You ok?” Lisa asked with concern.

“Uhh..yeah, I’m fine. I just felt kind of light headed for a minute.” He replied trying to think of a good excuse. He should be so excited to be seeing a very pretty girl in her bare minimums right? She was very beautiful with perky breasts and slender curves. As he observed her however, he was more envious that he himself did not look like that. He wanted those perky breasts and slender curves on his body! Oh how he wished that he could be a real girl.

Lisa slipped on the skirt and the cute top and did a model’s walk to get Jeffrey’s opinion.

“You’re right Lisa that looks amazing on you.” Jeffrey complimented.

“Thanks! If there is one thing I know its fashion. Try on my dress girl.” Lisa replied.

“Ok, I’ll be right back” He replonded as he grabbed the dress and headed into his bathroom.

“Oh we have a shy girl on our hands do we?”

“Yeah, I’m kinda shy” he replied as he closed the door.

He removed his clothes and stepped into the dress. It was so dang girly! He tried to adjust his bra straps to hide them under the dress straps but had a hard time because of the way the back crossed. He stepped out to model.

“Can you help me zip it up?”

“Oh, I already know I’m going to love you in this.” Lisa stated as she zipped the dress up in back.

“You look stunning Ashley. If Scott liked you before he’s going to find you irresistible now.”

Once again Jeffrey was filled with those warm, tingly butterflies. What was up?

“I adore this dress Lisa. It almost feels like I’m not even wearing a skirt.” He said as he swayed back and forth feeling the wind beneath the light fabric of the skirt.

“One thing though. We need to do something about your bra straps. You can see them on your back. Luckily I figured you would have this issue so I brought something to help.”

Lisa pulled out a cool little gadget that connected the straps of his bra and pulled them together to hide them under the dress.
“There ya go…pretty as a pony”

Lisa put on some white opaque tights as the night was expected to be chilly.

Jeffrey decided upon some nude, sheer pantyhose for the most elegant look. He felt daring and committed to putting them on in from of Lisa. He sat on the edge of the bed and bunched the nylon fabric in his hands slipping them on his pretty feet. He pulled them up to his knees all the while holding a conversation with Lisa. Standing up, he pulled them gradually up to his crotch then strategically turned around so that Lisa would not see any bulges. He finished by pulling the pantyhose up and snugly against his waist.

“Love the panties dear. Pink and blue go great together.” Lisa joked as she caught a glimpse of his lacy high cut pink panties. She had to give her friend a hard time since she found out that Jeffrey was shy.

“Stop it Lisa” Jeffrey replied once again turning bright red.

He slipped on his heels which had a substantial heel on them. Good thing he practiced a lot lately on walking in heels.

“I even brought a matching purse” Lisa said handing him the light blue hand bag with a thin shoulder strap.

The two girls walked out for Marge’s inspection.

“You girls look like princesses. No be good tonight ok?”

“We will auntie”

Jeffrey felt so pretty and feminine. Tonight he was truly a girl. His confidence was overflowing.
 
 
A short time later Scott knocked on the door.

“Ok Auntie, our ride is here”

Jeffrey answered the door.

“…you look beautiful” Scott gulped as he looked at the pretty girl.

Standing before him was a vision of beauty wearing a very tempting dress. She looked so dainty and delicate and he she was going out with him!

“Thanks, Lisa let me borrow this dress.”

“Cool, well it fits you very well” Scott replied as he mouthed ‘thank you’ to Lisa. Lisa smirked.

They hoped in the car with the girls in back and boys in front and headed to tgi Fridays for dinner. Lisa met up with her friend and Jeffrey gravitated towards Scott. All in all it was 8 people.

“Wow, you look amazing in that dress Ashley” Alicia said as the two hugged.

They squeezed into a large booth to enjoy dinner. Scott enjoyed the close quarters as Jeffrey leg brushed up against his. The dinner conversation was lively, comical and light hearted. This was living right here. Jeffrey really wanted to talk to Scott more but in this group setting it was a bit difficult.
 
 
After dinner they headed over to the movies where Scott once again refused to let Jeffrey pay. He blamed his mother for instilling those value on him.

He was being such a gentleman. Jeffrey thought it was so nice of Scott to always walk ahead to open the door for him. Jeffrey ran his hands under his dress to smooth his skirt as he sat down on the theater seat. As he crossed his legs he noticed how Scott’s eyes shot a glance at them.

Face it Jeffrey, it was very flattering that you made such a pretty girl that boy’s stared. There was something very self-fulfilling knowing that he was perceived by everyone as a cute teenage girl.

The two joked and giggled and were just having the best time. Never before did Jeffrey have a boy who he felt this close to. He gushed over all the attention he was flooded with.

The movie began and everyone focused on the film. It was a scary movie which everyone but Jeffrey knew was so that the guys could get closer to the girls to “protect” them.

Jeffrey did find the movie pretty scary. In fact, he was more frightened than he could ever remember. Was all this dressing as a girl affecting how he approached life?

Suddenly a character jumped out of nowhere startling everyone.

Jeffrey let out a yelp. He didn’t mean to but it just happened.

“You ok?” Scott asked somewhat joking.

“Yeah, sorry I just didn’t expect that.” Jeffrey replied feeling a little embarrassed.

“It’s ok, I’ll protect you” Scott answered as he reached his arm around Jeffrey and acted like he was holding back the villain on screen.

Jeffrey giggled at the whole situation as the two went back to watching the film. He noticed how Scott’s arm remained around his shoulder lightly grasping his arm. He glanced over at Lisa and Alicia and saw how the boys they were with were doing likewise. It was different for him though because he was really a boy. It wasn’t right for him to have another boy’s arm around him. It wasn’t fair to Scott. At the same time he had those warm tingly feelings again and didn’t want them to go away.
Tonight he was a girl and he would behave as a girl and just enjoy the moment.

He let the arm stay much to Scott’s joy.
 
 
The movie ended and as everyone walked out to the car it began raining.

“Oh crap, it’s raining!” one of them yelled as they began running to the cars.

“Come on, let’s go!” Scott said as he grabbed Jeffrey’s hand leading him quickly to the car.

Jeffrey held on tight feeling a strange sense of comfort and safeness with Scott holding his hand. He ran as quickly as his cute little heels would let him.
Scott opened the door and the two of them hoped in the back seat.

“Sorry, if I knew it was going to rain I would have brought an umbrella. Did you get too wet?” Scott asked the adorable girl.

“I’m ok, my pantyhose got a little wet by my heels but they’ll dry.”

“Well the rain didn’t harm your beauty at all…still pretty as ever.” He complimented Jeffrey.

“Thanks” Jeffrey replied blushing a beet red. He looked down and noticed that he was still holding Scott’s hand.

They headed for his cousin’s house which was a pretty big home. Jeffrey was very impressed.

“Can I get you some soda or punch?” Scott asked as he found a place on the couch for them.

“Punch please” he replied crossing his legs in a fashion that had become second nature.

He and Scott talked and joked and got to know each other more and more as the night progressed. Everyone there seemed to be enjoying themselves as the music played in the living room.

“This used to be my favorite song” Jeffrey interrupted Scott mid sentence to let him know how he liked the song that was playing.

“Oh yeah, used to?”

“Well I still really like it”

“In that case would you care to dance?” Scott replied standing up and holding out his hand.

Jeffrey was feeling brave and accepted the offer. He was surprised at how well Scott danced.

“Another thing my mom is responsible for. She said that girls like a guy who can cut the rug. Is she right?”

“Well you can sure cut the rug” Jeffrey joked. He loved how the skirt of his dress flowed and wrapped around his legs as he danced. Oh could this night get any better?

The next song came on and it slowed the whole mood down. A slow dance?

“Will you do me the honor?” Scott asked. Please say yes.

This was a big step for Jeffrey. He didn’t like boys so why would he want to be standing close to one while slow dancing. That would just be too close for comfort right? He didn’t like boys but he desperately wanted to be closer to Scott. What the heck? Just go with your feeling Jeffrey.

“Ok” he replied as Scott moved in close. Jeffrey instinctively put his arms around Scott’s shoulders and Scott arms wrapped around his waist.

Jeffrey felt goose bumps all over his body. He felt alive in Scott’s embrace! This wasn’t right was it? He focused on just enjoying the moment. The slow music played against the dim lights. Oh how romantic the setting was. Even with his heels on, he was a couple inches shorter than Scott. He was a girl. He was a girl. He was a girl.

The two talked lightly with Scott moving in close to whisper in Jeffrey ear. Each time he did Jeffrey felt shudders going down his spine. He was getting turned on. He was getting turned on by Scott. A boy! He had to get out of this situation but he felt trapped in the moment’s pleasure. If this was so wrong then why did it feel so very right?

Scott looked down on the beautiful girl. Her lips looked so shimmery and attractive. He looked at her and could see some possible interest as well. He leaned in once again very close to whisper in her ear.

As he leaned in, Jeffrey’s eyes became locked in Scott’s. It was irresistible. The heat of the moment had taken over and Jeffrey was helpless. For a split second he realized that what was happening should not be going on. Then his whole reasoning functions shut down. He was on pure instinct now.

Scott lips moved in close. Jeffrey wanted those lips against his! His eyes glazed over as his pretty painted eyelids closed and his lips waited for their prize. Then it happened. Jeffrey felt the gentle pressure of flesh on flesh. Scott’s lips were pressing against his! He grew weak in the pantyhose. What started as a light peck became a full kiss upon kiss. Jeffrey could not get enough as he relished Scott’s moist lips against his.

A moment paused for a breather and the two shared eye contact with each other. Scott smiled as did Jeffrey. Their lips met again in passionate embrace. As the kissing continued Jeffrey felt Scott’s hand move from his waist down to his ass. Scott was caressing his ass…and it felt magical! It was then that Jeffrey realized that he was very aroused as he felt his excitement growing in his panties. Crap!
 
 
Just then the song ended to Jeffrey's relief. Luckily the tightness of his pantyhose and the flowing fabric of his dress hid the erection underneath. He excused himself to the ladies room to gain his composure.

What just happened?!? He kissed a boy and went back for seconds! He was so turned on by Scott. He loved the way he walked, the way he talked, his rugged good looks. He was attracted to a boy! Oh wow, no matter how much he tried to deny the feelings he couldn’t. He liked boys! He was a girl right now though so he wasn’t really a boy kissing a boy right? So confusing! He straightened himself out and returned to the living room.

“You ok Ashley?” Scotts asked as Jeffrey returned.

“Yeah, I just got a little hot is all”

“That was amazing by the way.” Scott admitted referring to the long embrace.

“You too huh? This has been the best night of my life” he replied in a girlish glee.

Alicia and Lisa walked up to them.

“Hey you two love birds it’s time to go home. Rick’s parents are closing down the party.” Alicia said.

"Damn" Scott replied hoping that he could go back to kissing his rpetty friend.

"So you two seem to have hit it off pretty well" Lisa joked.

"You could say that" Scott replied.

Jeffrey blushed forgetting for a moment that he was not a girl. He blushed just as a young girl would.
 
 
And so the night ended with Scott walking Jeffrey to his front door.

“I had a great time Ashley and I hope we can do this again.”

“Me too” Jeffrey replied as Scott leaned in to give him another kiss.

Their lips met once again and fireworks went off. Jeffrey could not deny the pleasure.

“Ok…well…I ..uhh..I’ll see you later…ok…bye” Jeffrey nervously said in a girlish giggle. He was so flushed with emotion.

“Later Beautiful”

As Jeffrey entered his house and closed the door he realized that this is who he was. He was a girl. He enjoyed everything about being a female. He enjoyed the clothes, the makeup, the way he acted and yes, he enjoyed boys. Oh how he enjoyed boys!

He wasn’t sure what the future would bring and quite frankly the future scared him to death. One thing he was certain of however was that this night would forever be etched in his memory as the greatest night ever. No matter what happened or how difficult things would become, he would always have these magical moments to think back upon and keep him strong. I'm sorry, keep her strong.

Ashley was here to stay!

Now how would she break the news to her parents?

---

 
Finis~!